Trying to get a light and dark reaper to work together seems like a too literal angel and devil on Madison's shoulders.

I was initially skeptical that Madison was the first Timekeeper who would try and change the destiny of someone who was fated to do bad things, but when I thought about it I remembered that timekeepers tended to last centuries so it's entirely possible the previous keeper was a Calvinist who believed all of that was predetermined so trying to change it was useless and the keepers before that would be Pre-Calvinist. I seem to recall that early religions weren't big on choice so in that context I suppose it makes sense.

I have to wonder if one event can really reshape a person's entire destiny though. People who have near death experiences tend to be hyper aware and grateful for a period of time, but eventually life returns to normal, as it must.